(2R,3S)-3-bromo-N-phthaloylphenylalanine methyl ester | 132785-21-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2R,3S)-3-bromo-N-phthaloylphenylalanine methyl ester
• 英文别名: methyl (2R,3S)-3-bromo-2-(1,3-dioxoisoindol-2-yl)-3-phenylpropanoate
• CAS: 132785-21-8
• 化学式: C₁₈H₁₄BrNO₄
• 分子量: 388.217
• InChiKey: ZFRQHTZZHMIJDY-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3S)-3-bromo-N-phthaloylphenylalanine methyl ester 在 palladium on activated charcoal 氘代甲醇-d 、 氘 作用下， 反应 72.0h， 生成 (2S,3R)-<3-2H1>-N-phthaloylphenylalanine methyl ester 、 (2S,3S)-<3-2H1>-N-phthaloylphenylalanine methyl ester
  参考文献：
  名称：

  Synthesis of each stereoisomer of [3-2H1]phenylalanine and evaluation of the stereochemical course of the reaction of (R)-phenylalanine with (S)-phenylalanine ammonia-lyase

  摘要：

  The four stereoisomers of [3-H-2(1)] phenylalanine have been prepared. each as a single enantiomer in ca. 98% diastereoisomeric excess and with ca. 99% deuterium incorporation, by Side-chain bromination of phenylalanine derivatives, followed by deuteriolysis of each of the diastereoisomeric product bromides with deuterium over 5% palladium-on-carbon. The latter reactions, proceeded with retention of : configuration. (2R,3S)-[3-H-2(1)] Phenylalanine reacted with (S)-phenylalanine ammonia-lyase to give [3-H-2(1)] -trans-cinnamic acid, with 92% deuterium incorporation; while the (2R,3R) -stereoisomer of the deuteriated phenylalanine gave [3-H-2(1)] -trans-cinnamic acid with 27% deuterium incorporation. These results indicate that reaction of (R)-phenylalanine with the enzyme involves mainly loss of the 3-pro-R hydrogen and ammonia, in an antiperiplanar elimination process analogous to that previously reported for (S)-phenylalanine,while a minor pathway for reaction of :(R)-phenylalanine is either isomerization to (S)-phenylalanine; before elimination, or synperiplanar elimination.

  DOI：

  10.1039/p19940003545
• 作为产物：
  描述：

  (S)-methyl 2-(1,3-dioxoisoindolin-2-yl)-3-phenylpropanoate 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 为溶剂， 以40%的产率得到(2R,3S)-3-bromo-N-phthaloylphenylalanine methyl ester
  参考文献：
  名称：

  Stereocontrolled synthesis of β-hydroxyphenylalanine and β-hydroxytyrosine derivatives

  摘要：

  Side-chain bromination of N-phthaloyl-(S)-phenylalanine and tyrosine derivatives, followed by treatment of the product bromides with silver nitrate in aqueous acetone, affords the corresponding (2S,3R)-beta-hydroxy-alpha-amino acids, enantiospecifically and diastereoselectively. The diastereoselectivity depends on the carboxyl protecting group, tert-Butyl esters display greater stereoselectivity than the corresponding methyl esters, presumably as a result of a steric effect, while N-tert-butylamides react diastereospecifically due to a combination of steric and electronic effects.

  DOI：

  10.1016/s0040-4020(01)85256-x